Triethylamine → 6-Bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide

HRID 1677707ノート

反応式

HRID 1677707 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:18]([OH:20])=O)[C:5]2[CH:6]=[N:7][N:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:9]=2[CH:10]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH2:61][CH2:62][C:63]1[CH:68]=[CH:67][C:66]([S:69]([NH:72][CH3:73])(=[O:71])=[O:70])=[CH:65][CH:64]=1>CN(C=O)C>[CH3:73][NH:72][S:69]([C:66]1[CH:67]=[CH:68][C:63]([CH2:62][NH:61][C:18]([C:4]2[C:5]3[CH:6]=[N:7][N:8]([C:11]4[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=4)[C:9]=3[CH:10]=[C:2]([Br:1])[CH:3]=2)=[O:20])=[CH:64][CH:65]=1)(=[O:70])=[O:71]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 164609784-(Aminomethyl)-N-methylbenzene-1-sulfonamideHCID 581389136-bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid

生成物 1

HCID 444698036-Bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred room temperature solution of 6-bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid (0.25 g, 0.70 mmol) in DMF (15 mL) was added PyBOP (0.45 g, 0.90 mmol) and triethylamine (0.20 g, 1.6 mmol). After 15 minutes, 4-aminomethyl-N-methyl-benzenesulfonamide (0.15 g, 0.7 mmol) was added. After 5 hours, the reaction was quenched with water (30 mL), and extracted with ethyl acetate (30 mL). The combined organic layers were washed with brine (30 mL) and dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with a gradient of 30-50% ethyl acetate in hexanes to afford the title compound.

後処理

  1. waitAfter 5 hours
  2. customthe reaction was quenched with water (30 mL)
  3. extractionextracted with ethyl acetate (30 mL)
  4. washThe combined organic layers were washed with brine (30 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with a gradient of 30-50% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-e7cf63019dfc4d7491b6ce5c7d77d417
出典データセット
uspto-grants-2011_08
特許番号
US08008327B2

反応ノート

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